CAS: 1220979-75-8—Innovative probe reagent for sialic acid metabolism research

Sialic acid, as the key terminal sugar group of cell surface glycoconjugates, is widely involved in core biological processes such as intercellular recognition, immune regulation, pathogen infection, and cancer metastasis. 5-[(2-azidoacetyl)amino]-5-deoxy-sialic acid, as a chemically modified derivative of sialic acid, is an important tool molecule in the field of metabolic probe reagents. It provides a highly specific method for in-depth analysis of sialic acid metabolism dynamics, functional regulation and related disease mechanisms, and promotes the cutting-edge exploration of glycobiology and precision medicine.

Chemical Information

Chemical name: 5-[(2-azidoacetyl)amino]-5-deoxy-sialic acid

Common name: N-(2-azidoacetyl)-Neuraminic acid

Chemical formula: C11H18N4O9

Molecular weight: 350.28 g/mol

CAS number: 1220979-75-8

Category: Metabolic Probe Reagents

Structural features

Azidoacetyl modification: A 2-azidoacetyl group is introduced into the 5-position amino group of the sialic acid molecule. This azide group can be used as an efficient click chemical handle. It can be specifically covalently linked to alkyne markers (such as fluorescent dyes, biotin or isotopes) through copper-catalyzed or strain-promoted azide-alkyne cycloaddition reactions to achieve bioorthogonal labeling, thereby completing visual tracking without disturbing natural biological processes.

Deoxygenation design optimizes stability: The 5-position deoxygenation modification reduces the sensitivity of the glycosidic bond to enzymatic hydrolysis and enhances the metabolic stability of the molecule in the cellular environment. At the same time, it retains the nine-carbon sugar acid skeleton and carboxyl group of the core of sialic acid, ensuring that it can be recognized and utilized by metabolic enzymes such as sialic acid synthase and transferase, simulating the behavior of natural sialic acid in biological pathways.

Retain the functional skeleton of sialic acid: Maintain the basic structure of neuraminic acid, including the pyran ring configuration and hydrophilic side chain, so that the derivative can be integrated into the sugar chain ends of glycoproteins and glycolipids, and participate in sialic acid-related cell signaling and molecular interactions, providing a highly biologically relevant probe basis for research.

Main applications and advantages

Dynamic tracking and imaging of metabolic pathways

This compound can be used as a precursor analog for sialic acid biosynthesis. It is taken up by cells and integrated into the end of glycoconjugates through the endogenous metabolic pathway. With the click chemical properties of the azide group, it can be combined with alkynyl-modified reporter molecules to achieve real-time quantitative analysis of sialic acid metabolic flux, subcellular localization and live cell imaging. This capability allows researchers to visualize changes in the spatiotemporal distribution of sialic acid during development, differentiation, or disease progression, revealing regulatory networks of metabolic pathways.

Disease mechanisms and biomarker discovery

Abnormal sialic acid metabolism is closely related to various disease states, such as tumor metastasis, viral infection (such as influenza virus recognition), autoimmune diseases, and neurodegeneration. Through high-sensitivity labeling, this probe reagent can accurately detect changes in sialic acid modification patterns, abundance and localization under pathological conditions, help discover glycosylation biomarkers related to disease progression, and provide molecular basis for the development of drugs targeting sialic acid metabolism.

Drug screening and therapeutic target validation

In drug development, this tool molecule can be used to build a high-throughput screening platform to evaluate the inhibitory effect of small molecule compounds or biological agents on the activity of key enzymes in sialic acid metabolism (such as sialyltransferase or sialidase). Its labeling strategy allows rapid assessment of the impact of drug candidates on cell surface sialic acid expression, accelerating the early development and optimization of antiviral, antitumor, or anti-inflammatory therapies.

Basic glycoscience and functional research

As a core probe in glycobiological research, it promotes the systematic analysis of the structure-function relationship of sugar chains. Combining mass spectrometry, microscopy and omics methods, we can deeply explore the molecular mechanisms of sialic acid in cell adhesion, immune synapse formation, and pathogen-host interaction, while also providing technical support for the design of engineered glycoproteins and the development of synthetic sugar vaccines.

Advantages Overview

High specificity and bioorthogonality: The azide group is rare in biological systems, ensuring minimal background interference and extremely high signal-to-noise ratio in labeling reactions.

Metabolic compatibility and functional retention: Chemical modifications are performed at key sites, balancing the stability and metabolic feasibility of the probe, making the data more physiologically relevant.

Multi-functional platform compatibility: Adaptable to a variety of detection technologies, including flow cytometry, immunofluorescence, Western blotting and mass spectrometry imaging, supporting multi-scale research from in vitro enzymatic experiments to in vivo models.

Conclusion

5-[(2-azidoacetyl)amino]-5-deoxy-sialic acid is not only a chemical tool, but also a bridge between synthetic chemistry and complex living systems. From revealing metabolic homeostasis to decoding disease mechanisms, its value as a metabolic probe reagent is continuing to expand. With the rise of glycoscience in the therapeutic field, this compound will play an increasingly critical role in the development of innovative therapies, optimization of diagnostic strategies, and breakthroughs in basic science.

The above information is provided by the editor of KASONS and is for scientific research only.